The castle was constructed by contractors in 1897 for US$25,700 (equivalent to $941,000 in 2023) next to the natural deposit of yellow limestone which had been quarried by inmates of the preceding city workhouse jail across Vine Street.

The castle is two blocks south of the historic 18th and Vine, which has been referred to as America's third most recognized street after Broadway and Hollywood Boulevard due to the legacy of Kansas City jazz music.

Across the next five decades, the castle and surrounding field were periodically repurposed more than one dozen times including as a city storage facility, a Marine training camp, and a dog euthanasia center—abandoned in 1972.

The structure steadily accumulated trash, trees, graffiti, and a cascade of unproductive owners and investors including Bank of America and a convicted con artist.

Vagrancy was a class of petty crimes usually arising from a chronically degenerate lifestyle, resistance to employment and existing social programs, or just hard luck.

Citing a robbery at Edward Abbott's saloon at 117 Holmes St, the Kansas City Star reported, "The North end is recognized by the police to be the home of crooks.

[citation needed] For offenders who were too problematic for that help and who disobeyed police orders to vacate Kansas City, the legal system's last resorts were its main jail or a special court sentence into its workhouse.

The Kansas City Star outspokenly deplored the rotten frame shack with heavy boards nailed on the outside "to keep the prisoners from kicking holes through".

The cell room—"reeking with a thousand of different odors, with no sort of proper ventilation, and inhabited by millions of vermin of all sorts—was a place to turn the stomach of a sewer rat".

[14] A new facility was needed with greater capacity and scope: a high-security combined jail and workhouse, a decent standard of living, and a hard-core productivity program for serious offenders.

[citation needed] The Kansas City Star reported that the castle facility was expected to be less of a "terror" to inmates and more "thoroughly appreciated by the average hobo and that Major Alf Brant's boarders will at once begin to increase rapidly in numbers".

Superintendent Brant envisioned the castle's future beyond a workhouse jail, possibly eventually converted into "a reformatory of some kind"[14] or a hospital[16] by replacing the upstairs cells with rooms.

[14] On December 20, 1897, The Kansas City Times published an uncommonly huge cartoon and article declaring the new castle "Ready for Its Hobo Guests".

Upon arrival, Superintendent Alfred Brant admonished the filthy residents to a rigorous hygiene regimen, immediately giving them new clean clothes, thorough baths, and a new outlook.

[citation needed] As a part of their sentences, the women sewed prison uniforms and the men labored for the city's public works department.

Nation invaded M. A. Flynn's saloon at 117 East 12th Street,[7][18][19] chopping liquor bottles with her hatchet and standing tabletop to lecture patrons on their moral depravity.

Chief Hayes and Judge Brady had a deal that vagrants who defied police orders to leave town would spend one year at the workhouse.

The new man had reportedly been "peering in with a yearning and pie-eating appeal" after having quit his two jobs at a book publisher and at a maintainer of Yellowstone Park pleasure camps.

Weisflog's tenure had been reportedly "excellent" and he admitted that Dayhoff had legitimately won the job by virtue of the civil service competitive examination, but he slammed the table and said "Here I am and here I stay until my year is up or the court comes out with Battery B and tells me to vacate.

[22] Two days later on July 27, the two friends happily resolved at the mayor's office to a handoff on September 1, because time was needed for Weisflog to find a new house and for Dayhoff to make a business trip to Cuba.

Across the following five decades, the castle and surrounding field would be periodically repurposed more than one dozen times, including as a city storage facility, a Marine training camp, and a dog euthanasia center.

[15][27] This millennium made the castle a small token among colossal visions and broken promises of erasing Kansas City's epidemic blight.

In 2001, Bank of America pre-announced $46 million to redevelop 96 acres of blight across the Vine Street District but canceled in 2005 ahead of the global crash of 2008, selling much of it to KC native millionaire Ephren W. Taylor II who likened his invisible investments to the comic book antihero The Phantom.

Actually a con artist, Taylor promised in 2006 to develop his large Jazz District property into 42 homes plus a community center of museum in the castle, but was instead convicted of a Ponzi scheme defrauding Black churchgoers of millions of dollars and federally imprisoned.

This is presumptively backed by UrbanAmerica,[28][2] a company which in turn qualifies for up to 25 years worth of tax breaks by association with Eighteenth and Vine Redevelopment Corp., of which Dixon is the President.

[28] The city then discovered that Dixon had already been simultaneously under FBI investigation 2019 for allegedly committing financial fraud and death threats[28] while spending at least $20,000 of the Black Economic Union's money to pre-launch EVE.

This controversy also prompted the proposal of an upgrade to the city's Ethics Code to introduce background checks of applicants, and the resignation of a tax board member under concern of potential future conflict of interest due to his employment by UrbanAmerica.